Rudy Wins The Grand Prize

by the Troubador

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Heterosexual, Humor, .

Desc: Sex Story: A love story. Average joe wins sales contest and gets a trip to the Caribean. There things go cockeyed.

Reaching carefully from his stool at the bar, Rudy pulled the Hawaiian Sunrise up in front of him, stirring it gently with the little green umbrella. Holding the glass up to the sun he squinted through the bright colors now disbursing from the layers into which they had been poured. He tried to remember how many kinds of rum were there but gave up. Blearily staring at the collection of bar glasses in front of him, he wondered who the joker was that had been putting their empty glasses down in front of where he was sitting.

"Damn nasty thing to do" he thought. "The place was short handed, and the bartender seemed to have only enough time to make new drinks for the crowd, not to pick up the empties." Counting slowly he made it up to four empty glasses before losing count. Hiccuping, he almost fell off the stool. "Lucky," he thought to himself, "almost dropped my drink in the pool."

Swaying a little on the tall barstool, he cursed the wind that must be blowing to make him so unsteady when all he was doing was sitting quietly at the bar. He didn't want to stumble off the stool, placed as it was out in the center of the swimming pool. He had swum over here for a drink, but was dry now and figured he would walk back on the stepping stones that led to the patio from the bar.

Looking down at his baggy, tropical print bathing shorts he was amazed to see how dry they were. In the states he would have expected it to take several hours to dry so completely. Amazing how fast things dried down here in the tropical sun.

"Well, guess I'll go back to my cabana and take a nap before dinner," he mumbled. Easing slowly off the barstool Rudy drained the Hawaiian Sunrise then left the glass on the bar with all the others. Carefully stepping from stone to stone he made his way toward the edge of the pool. "Good Golly, Miss Molly," he thought, "these things must be floating to move around like this."

He was maneuvered to the next to last stepping stone when he began majestically swaying, pushing his arms out to the side where he slowly rotated them in large circles trying to balance. Onlookers later teased him that he had looked like ancient movie footage of the infamous Tacoma Narrows Bridge collapse, and nicknamed him Galloping Rudy. He twisted and turned, his movements becoming more and more uncoordinated before somehow managing to turn his arms one way, his body another and his knees an impossible third. Finally, seeming in slow motion, he toppled into the water, thinking as he fell, "Sure glad I didn't spill that drink!"

A minute later, the lifeguard fished him sputtering from the pool, and sent him on to his cabana with an attendant to make sure he got there all right.

Rudy was three days into the trip of a lifetime. His company had announced a sales contest for that summer. The Grand Prize, which nobody had ever won, was a two-week stay for two at a Caribbean Island Resort. It happened that was the summer everything Rudy had learned about his company, its products, and salesmanship suddenly came together.

Rudy had once been described as almost an average man. He wasn't quite tall, wasn't really athletic, but you couldn't say he wasn't tall or athletic. He just seemed to be kind of almost average. His sandy hair always seemed to be slightly disheveled, and though he had a nice wardrobe, his clothes seemed to be just a trifle mussed. Everyone was taken with his happy grin, which almost never left his face, and the girls all seemed taken by his twinkling eyes. He worked hard, but until the sales contest his supervisor's best description of the job he did was just about average. That was why Rudy was so excited about winning the Grand Prize.

Overnight Rudy found it was so much fun selling he wanted to do it 24/7. To his later astonishment that was almost what he did, for Rudy being single and unattached had no obligations at home. Clocking the greatest summer sales period the 100-year-old company had ever known Rudy won the Grand Prize.

Which gave him a problem. He not only didn't have a wife, Rudy didn't even have a steady girl. Certainly none of the girls he dated would even consider spending two weeks with him on a tropical island. For that matter there were none that he would consider asking to join him on a tropical island for two weeks. Actually, he never mentioned the trip to any of the girls he knew, being pretty shy. And he would be damned if he'd go off for two weeks on a tropical island with another guy. Although a couple buddies on his softball team hinted that it sounded like fun before saying, when he looked at them strangely, "Not that way, of course."

The problem was solved to his satisfaction when he talked the company into sending him alone for four weeks instead of him and a friend for two. He was proud of the salesmanship he used to talk them into losing their newly explosive salesman for a whole month. The clincher was pointing out that they would save hundreds of dollars on airfare if they only sent one person instead of the two they had budgeted for. The Vice President that had booked the trip at company rates didn't fight it too hard, he just took his secretary to Cancun again that year.

Rudy reached his island paradise Saturday afternoon, having left Friday afternoon and traveling the 'feeder line express' until climbing aboard the final leg on a flight out of Miami that morning.

Rudy had checked in, and begun checking out the ladies. Not surprisingly, all the women he saw were very firmly attached to men who were looking very proprietary. There were some real babes, along with some really nice looking older women he considered to be wives. He didn't know if the babes were wives or not and he sure wasn't going to ask.

Tired as he was, he didn't want to wait a moment to begin this dream. That was why he found himself falling into his cabana, a nice little bungalow a hundred yards from the main resort, and then crawling into bed. It was something he sure wasn't going to tell anyone about back home. That is, that he had been so bombed he fell through the door into his cabana and then had to crawl across the room and into bed.

Waking up the next morning he found fruit and juices had been delivered to his cabana before he awoke. It was a pleasant surprise to discover that whatever combination of fruits he had tried absolutely eliminated his hangover. Somehow he was never able to produce those results again.

He spent that day sightseeing and snorkeling. It was his first time in a snorkel mask, and it was even more fun than softball.

That evening Rudy enjoyed an elegant dinner and discovered the pool bar. It was stuck way out in the swimming pool, and it was obvious to Rudy only a wimp wouldn't swim out to get a drink. That evening he concentrated on Singapore Slings. Getting pleasantly mellow, he had a great conversation with some visiting Italians and went to bed after watching the sun fall into the sea.

Which led up to today. Rudy went snorkeling again that morning with a party from the resort. While in the water he met a party of Brits who had just arrived and were staying together in a large private bungalow about a mile down from his cabana. They all had a ball swimming, and the Brits joined him that afternoon at the pool bar. There they were joined by a quartet of nurses who also had just arrived from the states. When the Brits and nurses left to get dressed and ready for dinner Rudy had stayed for a few more drinks. That was when he began his experiment with the Hawaiian Sunrises and discovered other people were putting their empty glasses on the bar.

Rudy woke up in his cabana several hours later. He was still flying a little but anxious to get back to the resort for dinner. The Brits and nurses both had promised to be there for dinner and dancing. Rudy was darned sure looking forward to it.

The Grand Prize was looking like a real winner. Tonight was what two weeks in the Caribbean was all about. He was having a great time and to top it all off, he was going to be there an extra two weeks! Being honest with himself he didn't anticipate a bed partner. He was a pretty ordinary guy, and while the nurses were all great gals, good pals, they obviously wouldn't be into one-night stands. The Brits' women were all gorgeous but they were also very married and their men were there with them. The men were as big as their wives were gorgeous. Even more disgusting, they were nice people. "It didn't matter how great a salesman he was," Rudy told himself pedantically, "I couldn't do that to those nice people."

And that's how the evening went, up to a point. Sometime that night everything got cloudy. He remembered dancing a lot with one of the wives whose husband didn't like to dance. And he danced with the nurses. That memory black out cursed him the next morning.

Rudy awoke with a hangover. As he tried to focus his eyes on the ceiling it wouldn't stop moving long enough for him to accomplish the task. He rolled over to his left and almost fell off the bed in the process.

"This day is not getting off to a good start," he muttered to himself.

Rolling back onto his back, his right arm landed on something soft hiding under the covers. Looking over he saw blonde hair poking out from under the covers, then heard a sleepy moan coming from somewhere in that direction. The lump moved slightly and he felt a bare foot press against him as the movement stopped.

Maybe today wasn't going to be so bad after all!

Rudy stared at the figure lying next to him and tried to reconstruct the events of last night in his mind. This was not easy because the room kept spinning, and when he closed his eyes he felt as though he was floating on a stormy sea, bobbing up and down like a cork in a toilet. He instinctively reached out to steady himself and again made contact with the person sleeping next to him. This time the contact caused the person to stir briefly, and the covers fell off showing Rudy a contented female smile on an attractive face.

Rudy couldn't believe his eyes. He pinched himself to see if he was dreaming, but when he looked again she was still lying next to him. Last night must have gotten a lot more out of hand than he could have imagined! Gingerly slipping out of bed he unsteadily made his way to the bathroom. Taking three Excedrin in hand, Rudy staggered towards the kitchen to get something to drink - he didn't want to chance waking his bedmate with the sound of running water, whoever she was.

As Rudy opened the refrigerator door the phone rang. Almost simultaneously came a loud hammering on the door. The noises brought a loud groan from the direction of the bedroom and Rudy's head felt as though it was going to split open from the sudden noises.

Grabbing the telephone as it started to ring a second time he managed to croak, "Hello?"

"What the hell happened to you last night?" The shrill female voice coming through the receiver added to Rudy's headache. "I waited almost an hour before I decided you had left without me. Where the hell did you go?"

The knocking on the door turned to pounding, and a big male voice called out, "You better not try to hide from me, Rudy! I know you're in there, and I know who you're with. Open this door right now!"

As Rudy tried to sort out what to do next he felt a warm body press against his back. A warm, sultry voice whispered in his ear, "You certainly make it hard to sleep, lover!"

Trying desperately to think, Rudy babbled something into the phone about a household emergency and asked for the woman's telephone number, promising to call her right back. She hung up instead.

Then Rudy yelled at the door, wincing at the noise he made, "I'll be right there after I find my clothes." This announcement was met with hearty and vicious cursing from behind the closed door, and renewal of the hammering on the door.

Scooping the blonde into his arms, he kissed her soundly. It was a luscious smooch, but he was really trying to keep her silent. He sure as hell didn't want the gent outside to hear her; the man was violent enough already. Half running he stumbled with her back to the bedroom, only bouncing off the wall once. Plopping her on the unmade bed he tried to explain to her that there was an emergency and he had to get her out of the cabana without the guy outside seeing her. While explaining he took a very long look at the gal.

It was a pleasant look, as she hadn't bothered to put a robe on to come see him in the kitchen. More to the point, he recognized her as being at the party the night before, but couldn't remember whose wife she was. She was about average size, and all of her various parts fit together just right. He was particularly pleased to see she was not one of those girls who thought the half-starved look was chic. She certainly didn't carry any extra weight, but she was padded like a woman is supposed to be padded, giving her all the curves that turn men's heads, and other parts.

Luckily she had worn very little to the dance, none of which apparently included any kind of underwear, at least he couldn't find any, and he was able to slip her dress on over her head as she protested. Clothed, almost, she was a nice looking woman, but nothing spectacular except for the little glimmer of devilment in her eyes. He knew from looking at her that she would never be a beauty queen. Which wouldn't matter because she would be more fun to be around than a dozen of the hot looking girls.

Kissing her again, he made her promise to meet him poolside at 2:00 that afternoon. Flustered now and confused, she agreed as he helped her out the bedroom window. Then as he pulled on his pants he shuffled back to the front door to let his belligerent guest in, having only a little accident with the zipper.

He hadn't even been aware the doors could be locked until he got there and fumbled to get it open. The moment it was unlocked the man crashed it open, knocking Rudy backward onto his back on the wooden floor. He suffered a nasty crack on the head, and looked up from the floor at the biggest of the Brits. Thanking his stars that it wasn't the one they called Bruno, he tried to get up only to have the Brit plant a foot on his chest and command Rudy to stay where he was while he got his wife. Then the man disappeared into the bedroom, where he broke into another fit of cursing before thundering back into the living area.

With the Brit towering above where he was lying on the floor, Rudy couldn't figure out what the man was going to do next. Squinching both eyes shut he groaned weakly, "For God's Sake, if you're going to kill me, do it quick. This hangover is killing me already. Be merciful, be quick." Keeping his eyes squeezed shut he waited for the kicks and blows.

Instead, there was dead silence for what seemed like hours to Rudy, cringing where he was on the floor. Then came a low chuckle, followed almost at once by a deep laugh. Soon the man looming over him was holding his sides while tears ran down his face.

Rudy, deciding finally he was being allowed to die from hangover, opened his eyes and struggled to his feet. Standing there in only his trousers, he hesitated a moment then went to make coffee. Over his shoulder, he asked the Brit if he wanted to stay for a cup.

"This is going to sound strange," Rudy added, "but what's your name? My body is upright but my mind is still asleep, I'm sorry. And who is your wife?"

"Bloody hell, yank," the Brit answered, "I knew you had a skin full, but this is too much. I'm Peter, and my wife Julie and you were dancing last night; danced with her a lot. She was the medium tall blonde with hair down to her arse. The one with the red dress on, remember her now?"

The big man sat down at the table and buried his face in his hands and blurted, "I don't know where she's gone off to. She never made it home last night. It's not at all like her. I'm so scared something has happened to her... and then I thought since she was with you... and she dancing so much last night... and she enjoyed the gin as much as you I figured the two of you just... wandered over here never happened before she's never... been off over night before. I don't, know what might have happened to her! Buggers! My head hurts!"

"Well, let's get some coffee, and maybe a bite to eat, too, then go looking for her," Rudy offered. "I see my morning ration of fruit and juice is already here, help yourself."

Rudy dressed, and they sampled the bananas and papaya before heading out the door. Once outside Peter told Rudy that he walked to his cabana by following the road from the bungalow where he and the other Brits were staying. Rudy suggested they go back to the bungalow on the beach. It was a more pleasant walk and a little shorter, what with the way the road twisted and turned.

As they walked Peter kept telling Rudy, between moaning about how his head hurt, how worried he was. "Julie never disappeared before, it just isn't like her. If anything she keeps too close to me. I'm really worried about her, can't imagine what could have happened to keep her away."

They were just over half way to the bungalow when, about a hundred yards or so ahead, what looked like several bodies lying under the palm trees. Rudy and Peter sped their pace with Peter wondering aloud if that was his Julie. They soon found themselves running. Both men's faces were ashen as they got nearer.

There were indeed three bodies lying still under the palms.

As they neared the three figures, lying so still, Peter broke into sobs. Calling his wife's name he sprinted forward, throwing himself on the figure farthest from them. Just before Peter fell onto the poor woman lying so still, Rudy recognized that it was not the girl he had just helped out his bedroom window. He did recognize she was his dancing partner from the night before, the one whose husband did not dance.

He froze for a moment in horror, a moment suddenly broken by a loud, "Ooof!" as Peter landed on her chest.

"Oh, God! Help! Help! Rape! Fire! Help..." the erstwhile corpse began screaming while ineffectually beating at her captor's head and shoulders.

Peter leaped off the struggling woman, looking like a man who had seen a ghost. Then bending down he scooped the terrified woman into his arms, smothering her in kisses. The other two corpses stirred and the man lying in the middle clambered to his feet and he too began beating on Peter while trying to pry Julie out of his arms. For a moment the three wrestled, with Peter continuing to rain kisses down on Julie's terrified face and anything else of hers he could reach. The third body sat up, took a long look, and fell back down on her back, joining Rudy in gut shaking laughs. After a moment the three combatants slowed their separate assaults, took a good look at who they were fighting, and joined the others in laughter.

The woman Peter was holding so tightly definitely was not the one who had awakened that morning in bed with Rudy. Rudy wasn't sure if he was glad or not, Peter's wife was sure attractive.

Once everything was sorted out, the three bodies; Peter's wife Julie, Pauline, and her husband Steve, explained they had stayed at the resort long past when Peter had gone home, "... a bit the worst for drink" and after Rudy had, "... gone walking with his lady friend." They decided to stroll home on the beach. When they got tired, they sat down to rest a moment and enjoy the tropical dawn. They had fallen asleep, not to awaken until Peter had thrown himself onto his wife, almost scaring her into an early grave.

The Brits invited Rudy to another breakfast, and together they proceeded to their bungalow. Once there the five of them sat down to rolls, jam and coffee or tea.

Their talking and laughter soon had the other Brits awake and joining them at the table. Rudy kept his back to the door to the sleeping wing. If, when, the woman on the telephone came in, he didn't want her to think he was ignoring her because he didn't recognize her. She obviously had a real temper. At the same time he kept an ear cocked to warn him when she came. He was prepared to run if or when things got dicey. None of the women had the kind of voice he remembered hearing over the phone, and none of them gave him strange looks either. Well, none stranger than could be expected considering how the morning was going.

Walking back to his cabana Rudy tried to puzzle out who the blonde haired woman was that had spent last night in his bed. She hadn't been at the bungalow, so who in tarnation had he pushed out the window that morning? More important, considering the day so far, who was the mystery woman belonging to the voice on the telephone?

Rudy spent the rest of the morning breathing in the fumes of the tanning lotion he had slathered over his body, sitting on a lounger under a beach umbrella between his cabana and the sea and mulling over the strange events of the morning. The sun was gloriously warm, the breeze just right, and the smells from the jungle behind were heavenly. The sounds of the exotic birds in the jungle soothed his hangover and it slowly dissipated. Finally dressing just before noon, he meandered to the resort proper where he sat himself under a blue patio umbrella. Carefully judging the extent of his remaining hangover Rudy enjoyed a tropical salad, and ordered iced tea while breathing in the perfumes drifting on the air from the jungle and the visiting wives at tables around him.

After eating, he sat back to watch the breeze stir the palm trees as he mused on how the tropical vacation had gone so far. It was just beginning and he wondered how it was going to progress over the next three and a half weeks. Right away, he knew he would have to go easy experimenting with the other exotic drinks he saw on the menu. Back home he seldom had more than a single beer at one sitting. If he continued the pace he'd unintentionally been setting he wasn't sure if he would live to fly home. Although the Manila Moonrise did look interesting.

And who were the two mysterious ladies that had crashed into his life this morning? Try as he might, he couldn't remember enough of last night to help.

Shutting his eyes he could catch occasional glimpses of dancing with a lovely, fun blonde. In his memory she seemed to be different sizes at different times, and occasionally he almost, barely, caught a picture of Julie's proper and very pretty English face. But it was always laughing, never with that mind bending, smoldering look some women get at certain times. And he remembered that look coming from this morning's blonde. It didn't help that all the British wives were blond.

No, he was sure Julie and he had only enjoyed dancing and laughing together. Though he did seem to remember half carrying her off the floor one time and sitting her back down to the table late in the evening.

Trying to remember voices proved impossible, so he got nowhere in attempting figuring out who the woman on the phone had been. Rudy decided to just accept whatever his mysterious caller did when the mysterious caller finally showed up. Not that he had a choice.

He kept checking his watch, more frequently as it neared 2:00PM. As the magic, or was it fatal, hour approached for the blonde to meet him he grew morose and more and more nervous. He kept picturing three and a half weeks of sitting alone at the bar; maybe dancing with someone else's wife while the someone else was carefully chaperoning in the background. It wasn't the vacation he had been dreaming about.

He was lost in a cloud of 'dissipating hangover' self pity when he felt a tap on his shoulder. Turning he saw a medium sized blonde dressed in a loose-but-clingy soft yellow sundress with big red and burgundy flowers all over it. The girl had lovely blond hair, a plain-but-pleasant face and curves that were just right for the woman standing in front of him. A faint perfume captured his senses. As he was registering that she had really, really nice legs under that dress his eyes snapped back to her face and he saw the hint of devilment he had seen just that morning as he pushed her out the window.

Rudy stumbled to his feet, knocking his chair over in the process, and reached to put one hand on her shoulder, the other to shake her hand. Unfortunately he was off balance and found himself giving her a hard, full body hug instead.

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Story tagged with:
Ma/Fa / Consensual / Romantic / Heterosexual / Humor /